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3 Debated Questions

These are 3 questions that caused a stir when discussed them with some of my colleagues, so I need your feedback on them.

1- What is the difference between "few" and "a few"
and "little" and "a little"?
Some kept saying that "a few" is positive and "few" is negative, but that did not make sense to me.

2- which set is more correct:
student parkings or students parkings
library administration or libraries administration
company executives or companies executives
manuscript library or manuscripts library

Note that that we have several parkings, libraries, manuscripts, and executives, but someone told me it should be always singular because it's adjective here or something like that.
So is there a rule to follow in this case?

3- The use of the possessive apostrophe and s. :
-John's choices were limited - or- John choices were limited
- Guantanamo's dilemma -or- Guantanaom Dilemma

Someone said as long as you can add "of" in the sentence it should always have apostraphe. So, since you can say "the dilemma of Guantatnomo" its should be Guantanamo's dilemma.

I was using apostraphes well, until we had the debate and I got really confused and started making mistakes.

Re: 3 Debated Questions

1- I have few friends = I am lonely
I have a few friends= not many, but enough

2- Use the singular as it functions as an adjective. however, I'd say 'student parking spaces' or the first.

3- John's choices
With Guantanamo, I'd use the dilemma of Guantanamo- the dilemma is associated with Gitmo, but doesn't belong to it in the same way. 'Guantanamo's dilemma' is a possible phrase, but not likely to be used, but the 'Guantanamo dilemma' is fine.

Re: 3 Debated Questions

1- It would depend on the degree of urgency- removing the article would make things more urgent.
2- In a name, Association of Journalists might be preferred.
3- Philosophical, but here the characteristic is not meant to be a defining oe, but one that has been acquired from external forces, so it seems to me a fairly clearcut case os association.